In the Berkshires, summer camps in Lenox and Hinsdale rent to large groups outside their camp season, and a retreat property in Salisbury takes groups of about 60.
As of November 10, 2026, Large Group Stays lists 4 places in the Berkshires that sleep 15 or more people, from 64 to 500 guests. 3 sleep 100 or more. The largest is YMCA Camp Hi-Rock in Mount Washington, MA, which sleeps 500, per its operator.
Distances are straight-line from the closest place we list in Berkshires, so the drive will be longer. Group pick means the business publishes a group rate, private booking or buyout. Group details come from each business's own page, checked Nov 9, 2026. Entries marked "group terms not checked" are nearby parks and attractions from Wikidata. Confirm prices and group sizes before you book.
Market 32Supermarket · 495 Pittsfield Road, Lenox · about 3.8 mi from the closest listing
Guido's Fresh MarketplaceSupermarket · 1020 South Street, Pittsfield · about 4.0 mi from the closest listing
Stop & ShopSupermarket · 1 Dan Fox Drive, Pittsfield · about 4.0 mi from the closest listing
Market 32 by Price ChopperSupermarket · 555 Hubbard Avenue, Pittsfield · about 4.1 mi from the closest listing
Stop & ShopSupermarket · 660 Merrill Road, Pittsfield · about 4.4 mi from the closest listing
AldiSupermarket · 898 Crane Avenue, Pittsfield · about 4.6 mi from the closest listing
Big YSupermarket · Pleasant Street, Lee · about 4.6 mi from the closest listing
Stop & ShopSupermarket · 2 North Elm Street, North Canaan · about 5.6 mi from the closest listing
Big YSupermarket · 200 West Street, Pittsfield · about 6.7 mi from the closest listing
IGASupermarket · 2628 Anthony Street, Town of Hillsdale · about 7.0 mi from the closest listing
Guido's MarketplaceSupermarket · 760 Main Street, Great Barrington · about 7.8 mi from the closest listing
Big YSupermarket · 700 Main Street, Great Barrington · about 7.9 mi from the closest listing
Store locations from OpenStreetMap contributors (ODbL). Check hours before a big shop. For delivery, enter the rental's address in the store's app or Instacart to see if they deliver there.
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